The diving in Key West is great, year round. Temperatures range from 86F in the summer to about 73F in the coldest months (I'd say January-March), depending on the depth you like. Visibility is generally about 50', but there is a large range. You can see a lot of sea life, especially at the marine sanctuary at Looe Key. There are also quite a few wrecks, many sunk intentionally as artificial reefs. If you're into tech diving, you can find opportunities for that too; wrecks between 140' and 350', including a submarine. Best sea life I have seen: Sharks, dolphins (like flipper, not mahi-mahi), turtles, spiny lobster, moray eels, sting rays, jewfish. Not many opportunities for shore diving, so weather is a limiting factor. Winds much greater than 15kts cause problems.
When you're not diving, Key West is a great place to hang out. Duval Street has a large number of bars, and they are all great. The beer is cold and the people are friendly. There are also historical places if you're more the library type than the bar type. You can see Harry Truman's Little White House, and Papa Hemingway's House on Whitehead Street. You can take a trip on a historical schooner, or check out the sunset ceremony nightly, year-round, at Mallory Square - lots of street performers; jugglers, magicians, comedians, and a silver guy.
Key West has a small airport, or you can drive down from the mainland. It is about 3-4 hours from Miami, a great drive down US1, across a bunch of bridges. Beautiful sight, do it in the daylight if you can.
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French Angelfish, Pomacanthus paru.
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Spotted Scorpionfish, Scorpaena plumieri.
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A mixed medely school of fish swim through a short overhang.
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A Bicolored Damselfish hides inside a Vase Sponge with Corky...
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Scrawled Filefish, Aluterus scriptus.
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